Mercury derivative of nitro-metacresols



,15 fact that mercury derivatives" of .nitro-metangZO known ,25 formula:

{40 This'is then converted into an anhydro-hydroxy- 300 0., may be represented by the formula:

5 The halogen derivatives are formed by treatand employing themethod' and quantities de- "Patented Sept. 26,1933 v 1 MERCURY ramas 0F m me-M TA; censors" Geoige WQRaiziss and: Le any W1 oim'en) 1 Philadelphia, Pa., assignors to Abbott Labora tories, North Chicago, I ll., ;a corporation ,of,

5 Illinois o sawing. ApplicationDecember 4,1931

sen rmsvam'z, 1 wimma -1 Our invention relates to certain new coming either the *ac'eto'xy, hydroxy or 'anhydro-- pounds which have been found to be especially hydroxy'derivatives with a halide acidthus; effectiveas bactericidal and bacteriostatic agents, y l particularly in combating infectious diseasesfand f%N%ggg+gg%Zi+ H o 355 relates more particularly, to mercury derivatives 1 1 l, l 313. 1 @g l of nltro-cresols. p I The nitro "derivativesflofmeta-cresol tend to Y I In Raiziss Patent No. 1,554,293, granted Sepform di-mercury compounds even when using tember'22, 1925, andreissu'edas No. 17,563, dated only one moleof mercuric acetate as above, ex- ,January 14, 1930, and"in'Raiziss, Patent No. cept in the case of fienitro-rneta-cresol which 1 1,630,072,,granted May 24, 1927, there are deforms'a mixture of mono-mercury and di- -merscribed certain mercury derivatives of nitro lcurycompounds. This possibility is eliminated,

ortho-cresol. These derivatives were found to however, if two males (114 g.)'- of mercuric acehave excellent properties asfbactericides. Howtate are used, resulting in formation of only diever, our continued research has developed the acetoxy-mercuri-nitro meta-cresols.

cresol and their variousisomersmaylikewisebe y M prepared and that certain of these last men-- --2 7L 5Jgrams of,dmitroimeta-cresol preparedby I tio'ned 1 derivatives possess markedly "superior nitrating meta-cresol in acetic acid medium :at

properties to" those'of the derivatives previously low temperature 5 to +8? 0;. l(Beric hte--42,

3098) Jaredissolvedjin 15.4 grams of NaOI-I and Z5 These new nitro-cresol derivatives difier from 1200 cc. of H20. To this isadded 114 grams of I each other, sometimes to {a considerable extent, mercuric acetate dissolved in420 cc. ofwaterand' in their physical, chemical and 'bacteriological'f 24 CCyOf acetic acid. The mixture is boiled until properties, and maybe representedby the typical the nitro-cresol is completely mercurated, this being determined byremoving a small portion of R a both precipitate and solution from the reaction y x w g. t mixtureandadding to this a solution of sodium forthemono-mercury derivatives, and g hydroxide; w clear yellow. to orange red l X j solution is obtained the mercuration is complete.

- 0 I l Y l {The mixture is cooled and filtered, The dried for t -m u y de fi s;wh i R' precipitateisthen dissolved in boiling-acetic sentsany of the isomers of nitro-meta-cresol acid, usingsufiicient acid to obtain a clear solu and X represents an acetoxy group, CHaCOO-ytion, which;- is filtered and ,cooled. Crystals. of

a halogen, a hydroxygroup ;OH, or when a di-acetoxy-merc uri-nitroecresol separate, This; moleculeof water'isrremove'd from the latter, an is repeated twice and the final batchof crystals anhydro-hydroxy group O,-. is washed with acetone and dried. In preparing these new products, we mercu The product, 2,6-diacetoxy-mercuri-d-nitrorate any of the isomers 'ofa nitro-meta-cresol -meta. cresol, consisting of pale yellow needles I and produce first an acetoxy-mercuri compound. darkening at 240 C. and not meltingbelowi mercuri derivative according to the following reactions:

The hydroxy-mercuri derivatives are formed l I l I @59 preferably as alkali metal salts in alkaline solu- I I ,951]

tion, as follows: a I a Example) y j I CeHaClHa.NOzOHHgCOOCHe HNaOI-lk Using Pmpared'by diazcti' zation of meta-toluidine andsubsequent decom-' C6H2CH3-NO2'oNa'HgOH+CH3'COONa+H2O position in dilute nitric acid (Berichte-42 309s) scribed in Example 1, we obtain 4,6-diacetoxymercuri-2 -nitro -meta-cresol:

. I 0H .OOO.Hg ND;

Haoodom This product consists of pale greenish-yellow needles, darkening at 290 Q not melting below 3000 C. V 1. l

The compounds describedabove are' usually dispensed in the form of their sodium same: in aqueous solution,the preparation of which will be obvious to those skilled inthe art.

Nitro-meta-cresols ordinarily do not form monomercury derivatives, but on mercuration oi 6-nitro-meta-cresol using one mole of mercuric acetate, ..a material .was obtained which, on an attempt to recrystallize it from aceticacid, did not completely dissolve in the amount of acetic acid used. The small amountofinsloluble material was crystallized independently from acetic n oocbrn Changes and variations' coming within the spirit' of our invention will doubtless Sug est themselves to those skilled in -the 'art. Hence, we 40 do not wish to be-limited to the specific embodiments disclosed herein or uses mentioned except to the extent set forth in the appendedclaims;

which are to be interpreted as broadly as the state of theartwill permit.

"We'claim as our invention.

'1. Amercury compound of a-nitro-meta-cresol, said composition being characterized -in that it is of high bactericidal value. 1

V 2. A mercury derivative of a nitro-meta-cresol,

' represented by the fQrmuIa RQIgXJm, where R repre'sentsthe nucleus of a nitro-meta-cresol, X represents a group from theclass consisting of acetoxy, a halogen, 'hydroxy,- and anhydrohydroxy, and n represents a whole number :not

gleater'thanz. a 1

3. An acetoxy-mercuri derivative of a nitrometa-cresoi, said composition being characterized in that it is of high bactericidal value.

4. A mercuri derivative of -nitro-meta-cresol, saidicomposition being characterized in that it is of high bactericidal value.

5. Diacetoxy mercuri 4 nitro meta-cresol,

which may be represented by the structural formula:

orncoor H coccm y V J M NO: '1: Diacetoxymercuri 2 -nitro-meta-cresol, which may be represented by the structural formula:

- on; I

C1 1 aC OO;Hg N02 Hg.QOC.CH: 7. 4-acetoxy mercuri -.6 nitro meta-cresol, whichemay be represented:v v I 7 r Hg.OOO.CH= 18'. A mercury derivative of a'nitro-meta cresol represented most probably by the formula Y Y Y Y ox groups being ortho or para to the hydroxyl.

GEORGE W. RAIZISS. LEROY W. .CLEMENCE. 

